Anisole → HCID 18962093, compound

Participants

Reaction Conditions

Reaction Steps

Suspend sodium hydride (48 mg, 2 mmol) and anisole (215 mg, 2 mmol) in anhydrous dimethylformamide (2 mL), cool to 0° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution 1-[(3,5-di-t-butyl-4-hydroxyphenyl)]-1,5-bis(t-butyloxycarbonyl)-1,5-diazapentane (1.91 g, 4 mmol) in dimethylformamide (2 mL). Stir until evolution of hydrogen ceases. Add, by dropwise addition, a solution of 1,5-dibromopentane (230 mg, 1 mmol) in dimethylformamide (2 mL). Stir overnight at room temperature then carefully quench with saturated ammonium chloride. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound.

Provenance & Evidence